- Synthesis of chiloglottones - Semiochemicals from sexually deceptive orchids and their pollinators
-
A five-step synthesis of monoalkyl- and 2,5-dialkyl-1,3-cyclohexanediones (1) is described via a sequence involving sequential Birch reductions and alkylations from the readily accessible and inexpensive starting material, 3,5-dimethoxybenzoic acid. Two approaches were considered in which alkylation at C-2 occurs either prior or subsequent to the proposed reduction. The successful route, in which Birch reduction of a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed for their biological activity via electroantennographic detection.
- Poldy, Jacqueline,Peakall, Rod,Barrow, Russell Allan
-
supporting information; experimental part
p. 4296 - 4300
(2009/12/06)
-
- Preparation of Some 1-Alkyl-4-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylic Acid Ester and Amide Herbicides by Reductive Alkylation of 3,5-Dimethioxybenzoic Acid
-
Reductive alkylation of 3,5-dimethoxybenzoic acid with haloalkanes afforded the 1-alkyl-3,5-dimethoxycyclohexa-2,5-diene-1-carboxylic acid derivatives (3a-e) which, upon esterification and hydrolysis furnished methyl 1-alkyl-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (4f-j).Reaction of (4f-j) with butyric anhydride gave methyl 1-alkyl-4-butyryl-3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (6a-e) which were converted into methyl 1-alkyl-4--3-hydroxy-5-oxocyclohex-3-ene-1-carboxylate derivatives (2a-e).Similarly, the oximeO-ether derivative (2f) was prepared from the amide (4l), obtained from reaction of (3b) with N,N'-carbonyldiimidazole and dimethylamine followed by hydrolysis.
- Liepa, Andris J.,Wilkie, John S.,Winzenberg, Kevin N.
-
p. 1217 - 1225
(2007/10/02)
-
- Synthesis and activity of 5-(aminomethylene)-1,3-cyclohexanediones: Enolic analogues of γ-aminobutyric acid
-
Eight 1,3-cyclohexanediones with an aminoalkyl side chain in the 5-position were synthesized as rigid enolic analogues of GABA (γ-aminobutyric acid). Biochemical investigations about their abilities to displace [3H]GABA and [3H]baclo
- Mann,Humblet,Chambon,Schlichter,Desarmenien,Feltz,Wermuth
-
p. 1440 - 1446
(2007/10/02)
-
- Studies on Terpenes. 8. Total Synthesis of (+/-)-Linderalactone, (+/-)-Isolinderalactone, and (+/-)-Neolinderalactone, Germacrane Furanosesquiterpenes
-
The synthesis of linderalactone (1), isolinderalactone (2), and neolinderalactone (3) is described and exploits the unique ability of these fluxional systems to enter into Cope and abnormal Cope rearrangements.The symmetrical β-diketone 10 was converted i
- Gopalan, Aravamuden,Magnus, Philip
-
p. 2317 - 2321
(2007/10/02)
-